Imidazole → (4-Bromo-2,6-dimethylphenoxy)(tert-butyl)dimethylsilane

HRID 1297773Notes

Reaction equation

HRID 1297773 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([OH:9])=[C:4]([CH3:10])[CH:3]=1.N1C=CN=C1.[C:16]([Si:20]([CH3:23])([CH3:22])Cl)([CH3:19])([CH3:18])[CH3:17]>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([O:9][Si:20]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:23])[CH3:22])=[C:4]([CH3:10])[CH:3]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 169194-Bromo-2,6-dimethylphenolHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 14959500(4-Bromo-2,6-dimethylphenoxy)(tert-butyl)dimethylsilaneYield 86.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve 4-bromo-2,6-dimethylphenol (30.16 g, 150 mmol) and imidazole (26.6 g, 390 mmol) in CH2Cl2. Added t-butyldimethylchlorosilane (36.17 g, 240 mmol) and stirred mechanically for 3 h. The solids were vacuum filtered and the filtrate concentrated. Suspended the resulting residue in water and extracted with ethyl acetate (2×150 mL). The combined organic portions were washed with water (150 mL) and brine (150 mL) and then dried (Na2SO4), filtered and concentrated in vacuo to give a light brown oil. Purify on a Waters Prep 2000 LC (hexanes) to give 40.96 g of the title compound as a clear liquid. 1H NMR(CDCl3): δ6.91 (s, 2H), 2.00 (s, 6H), 0.86 (s, 9H), 0.01 (s, 6H).

Workup

  1. filtrationfiltered
  2. concentrationthe filtrate concentrated
  3. extractionextracted with ethyl acetate (2×150 mL)
  4. washThe combined organic portions were washed with water (150 mL) and brine (150 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give a light brown oil
  9. customPurify on a Waters Prep 2000 LC (hexanes)

Sources & evidence

ORD record
ord-e421707b51de41d28c5b0271bf26fe70
Source dataset
uspto-grants-2007_07
Patent number
US07250442B2

Reaction notes

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